The chemistry of Pineapple

THE HISTORY OF pineapple AROMA FORMULATION

The exotic sourness of the aroma of pineapple, whose key constituents have been identified, attracted some interest from flavor formulators in Europe in earlier times. However, the public remained rather indifferent towards it.

The old formulations used amyl and ethyl butyrates to make up more than 50% of the composition, and a small amount of deterpenated lemon, citral, or vanillin (2% of the total formula).

Later, still using amyl and ethyl butyrates as a base, the formulas became even more intricate and involved a wider variety of ingredients. Butyric acid, amyl and ethyl acetate, acetic aldehyde, allyl caproate and caprylate, ethyl caprylate, and orange and angelica essential oils were all used, as well as a range of other natural and synthetic compounds. This combination of elements achieved a complex and unique flavor that was highly sought after. The exact combination of ingredients varied depending on the desired flavor profile, but the use of amyl and ethyl butyrates as the base remains a unique and essential part of the formula.

Formulators who studied allyl cyclohexyl propionate and allyl phenoxy acetate, among other compounds, made further advances in the formulation. This led to compositions containing, for example, ethyl isovalerate (18%), ethyl butyrate (18%), allyl heptylate (14%), butyl acetate (10%), allyl caproate (10%), ethyl propionate (8%), allyl cyclohexyl propionate (6%), ethyl heptanoate (6%), allyl phenoxy acetate (1%), amyl acetate (2%), and a combination of orange and lemon essential oils and vanillin.

Such a formulation is interesting because it uses allyl cyclohexyl propionate and ethyl phenoxy acetate, products not found in nature, alongside ethyl isovalerate and ethyl butyrate, which are essential constituents of natural pineapple flavor.

By examining the various flavoring substances found naturally or synthetically, we can create a partial list of products that can be used to add pineapple notes to a formulation.

Belonging to the first group are decyl acetate, butyl isobutyrate, methyl allyl caproate, cinnamyl acetate, n-butyl acetate, hexyl butyrate, propyl isobutyrate, methyl B-methyl thiopropionate. Additionally, bornyl acetate may be of interest due to certain nuances.

The second list includes allyl cyclohexyl acetate, allyl cyclohexyl butyrate, 2-allyl nonylenate, ethyl hexadienoate, methyl undecylenate, allyl undecylenate, and isoamyl isobutyrate.

It is advisable to consult the positive lists drawn up by the relevant health departments in each country before using the above products.

Since 1945, Haagen-Smit and coworkers have made significant progress in studying the composition of pineapple aroma. Based on the most recent work, we list the constituents that have been definitively established.

• Methyl acetate

• ethyl acetate

• ethyl acrylate

• methyl n-butyrate

• ethyl n-butyrate

• methyl a-valerianate

• methyl isovalerianate

• ethyl lactate

• ethyl isovalerate

• methyl n-caproate

• methyl isocaproate

• ethyl n-caproate

• methyl n-caprylate

• ethyl n-caprylate

• n-amyl n-caproate

• methyl b-methylthiopropionate

• ethyl 3-methylthiopropionate

• acetic acid

• methanol, ethanol

• n-propanol

• isobutanol

• n-pentanol

• acetone

• formic aldehyde

• acetic aldehyde

• diacetyl

• furfural

• methyl n-propyl ketone

• 5-hydroxy-2-methylfurfural

• 2,5-dimetil-4-idrossi-3-(2H)-furanone

• p-allylphenol

• y-caprolactone.

---

Sources and Information

• Fulvio Ciccolo — Scentspiracy 2023

• Professor G Fenaroli, Aromatizzazione 1969

• Photoby Hello I'm Nik, Julien Pianetti on Unsplash